Fourteen years into stand-up, Big Jay has emerged as one of our foremost storytelling comics. "It's a kind of a combination of storytelling mixed in with talking to the crowd. I do that a lot," he says. It's those crowd interactions that will often spark a story from his vast repertoire.

But, of course, storytelling requires the audience to take a journey — and occasionally they're not on board.

That doesn't bother Oakerson. "One of the greatest milestones I hit as a comedian," he explains, "was when I realized I wasn't afraid of the silence on stage, and still owning the stage. I now have no fear of any kind of awkwardness on stage: I embrace it."